In this episode of Inside the Workflow, we dive into a conversation with Ben Rosenberg, the Senior Director of Customer Support, Enablement, and Community at ChurnZero. With a background spanning hospitality, finance, and SaaS, Ben brings a wealth of knowledge to leading customer experience teams. His focus on leadership, mentorship, and a human-centered approach has made him a standout in his field. Here’s a closer look at the insights Ben shared during our conversation.
From Hospitality to SaaS: Ben’s Career Journey
Ben’s professional journey began in hospitality and retail before transitioning into financial services at Charles Schwab, where he developed a passion for customer experience.
“I’ve always loved helping people. My time at Schwab helped me see how rewarding it is to solve problems and guide customers through complex issues.”
Today, Ben channels that same passion into his work at ChurnZero, overseeing customer support, enablement, and community-building efforts. His philosophy centers on creating positive experiences and ensuring customers feel supported at every stage.
Leadership Style: Balancing Transparency and Adaptability
Ben’s leadership approach is rooted in flexibility, transparency, and fostering trust within his teams.
“There’s no single best leadership style. The most effective leaders adapt their approach based on the situation.”
He encourages his team to embrace diverse perspectives, valuing agreement and healthy debate.
“I’m big on transparency. Ninety-nine percent of what I know is worth sharing. The more my team understands our decisions, the more aligned we are.”
Ben also emphasizes the importance of maintaining a united front after discussions, ensuring the team moves forward cohesively.
What Energizes Him: People, Problem-Solving, and a Love for Learning
Ben thrives on leadership development and mentorship.
“Helping people grow in their roles and sharing what I’ve learned is one of the most rewarding parts of my job.”
Outside of work, Ben’s hobby of woodworking has taught him valuable lessons about patience and learning from imperfection.
“Woodworking has shown me that you don’t have to be perfect to make progress. It’s okay to make mistakes as long as you learn from them.”
Industry Insights: Challenges and Emerging Trends
Ben is keenly aware of the evolving dynamics in customer support and enablement, particularly in SaaS.
The Shift Toward Digitization
With the rise of automation and AI tools, companies are exploring ways to serve customers more efficiently while maintaining a human touch.
“AI tools are getting better, but for B2B scenarios, they’re not quite there yet. Human-led support might become a competitive advantage in the future.”
Balancing Revenue and Engagement
Ben notes the ongoing debate within customer success about prioritizing revenue versus adoption and engagement.
“The most successful teams strike a balance. Revenue ownership is important, but so is ensuring customers adopt and benefit from the product.”
The Future of Customer Success
Ben sees the industry moving toward greater specialization and leveraging AI to supplement human efforts.
“The next big challenge is figuring out how to serve SMB customers effectively at scale without losing the personal touch.”
He also predicts that tools enabling deeper relationship insights and smarter automation will redefine how customer success managers work.
“Our goal is to use AI to make CSMs’ jobs easier—serving them the information they need so they can focus on building relationships.”
Personal Philosophy: Staying Curious and Customer-Centric
Ben’s advice to aspiring professionals centers on curiosity and customer focus.
“Be curious and learn about every part of the business. Great CSMs succeed because they genuinely care about their customers and are willing to get creative with solutions.”
He encourages leaders to prioritize understanding team challenges and fostering collaboration across departments.
“The best leaders listen and look for ways to help. When you show that you care, people respond.”
Conclusion: A Leader Committed to Growth and Connection
Ben Rosenberg’s journey and insights remind us of the value of adaptability, transparency, and a human-centered approach. Whether he’s mentoring a team member, refining a customer process, or crafting a piece of woodwork, Ben exemplifies the power of continuous learning and a commitment to excellence.
